Hydrochloric Acid → HCID 18472282, Verbindung

HRID 566097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566097
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.[SH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[S:11][CH2:12][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21625Ethyl 3-mercaptopropionateHCID 7363275-Bromo-2-fluorobenzaldehyde

Produkt 1

HCID 18472282HCID 18472282, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-2-fluorobenzaldehyde (0.49 g, 2.62 mmol) and ethyl 3-mercaptopropionate (0.37 ml, 2.88 mmol) in N,N-dimethylformamide (10 ml) was added potassium carbonate (0.90 g, 6.55 mmol), and the mixture was stirred at room temperature for 1 hour and then at 70° C. for 15 hours. The mixture was poured into ice-water, and made pH 4 with 1N hydrochloric acid. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with magnesium sulfate. The solvent was evaporated, and the residue was purified with silica gel column chromatography [hexane:ethyl acetate (5:1)] to give ethyl 6-bromo-2H-thiochromene-3-carboxylate (0.45 g, 58%) as yellow powder, a part of which was recrystallized from ethanol to give pale yellow needles.

Aufarbeitung

  1. waitat 70° C. for 15 hours
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography [hexane:ethyl acetate (5:1)]

Quellen und Nachweise

ORD-Eintrag
ord-9dbcbe6f74384122a3d6f728c71ce38a
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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